| Description |
1 online resource (xiii, 488 pages) : illustrations |
| Series |
Topics in heterocyclic chemistry, 1861-9282 ; 26 |
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Topics in heterocyclic chemistry ; 26. 1861-9282
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| Contents |
Note continued: 1. Introduction -- 2. Dyes and Pigments -- 2.1. Textile Dyes -- 2.2. Dyes for Human Use -- 3. Agriculture -- 4. Animal Health -- 5. Over-the-Counter Drugs -- 5.1. Dietary Supplements -- 5.2. Nutraceuticals -- 6. Essential Oils -- 6.1. Flavor Enhancers -- 6.2. Perfumes -- 7. Summary -- References -- Electrophilic Substitution Reactions of Indoles / Richard J. Sundberg -- 1. Introduction -- 1.1. Experimental Measures of Reactivity -- 1.2. Theoretical Measures of Reactivity -- 1.3. Application of Electrophilic Substitution in Synthesis -- 2. Protonation and Acid-Catalyzed Oligomerization -- 2.1. Equilibrium Protonation -- 2.2. Acid-Catalyzed Oligomerization -- 2.3. Acid-Catalyzed Cyclization -- 2.4. Enzymatic Protonation -- 3. Halogenation and Related Reactions -- 3.1. Fluorination -- 3.2. Chlorination -- 3.3. Bromination -- 3.4. Iodination -- 3.5. Synthetic Applications of 3-Haloindolenine Intermediates -- 3.6. Enzymatic Halogenation -- 3.7. Sulfenylation, Thiocyanation and Cyanation -- 4. Friedel-Crafts Alkylation -- 4.1. Benzylation -- 4.2. Allylation and Prenylation -- 4.3. Alkylation by Electrophilic Alkene Activation -- 4.4. Intramolecular Alkylation -- 5. Alkylation by Carbonyl Compounds -- 5.1. Indol-3-yl Carbinols -- 5.2. Bis-Indolylalkanes and Related Compounds -- 5.3. Tris-Indolylalkanes -- 6. Alkylation by Conjugate Addition -- 6.1. Catalysts for Conjugate Addition -- 6.2. Enantioselective Conjugate Addition to Enones -- 6.3. Reactions with Enediones and Dienones -- 6.4. Reactions with Alkylidene Malonates -- 6.5. Addition with Nitroalkenes -- 6.6. Other Conjugate Addition Reactions -- 6.7. Intramolecular Conjugate Addition -- 6.8. Conjugate Addition with Intramolecular Nucleophilic Capture -- 7. Aminoalkylation (The Mannich Reaction) and Amidoalkylation |
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Note continued: 7.1. Modified Reaction Conditions -- 7.2. Enantioselective Reaction Conditions -- 7.3. Intramolecular Aminoalkylation: The Pictet-Spengler Reaction -- 7.4. Bischler-Napieralski Reaction -- 8. Acylation -- 8.1. C-3 Acylation -- 8.2. C-Ring Acylation -- 8.3. Intramolecular Acylation -- References -- Reactions of Indole with Nucleophiles / Tara L.S. Kishbaugh -- 1. Introduction -- 2. Nucleophilic Additions to Indoles -- 2.1. Nucleophilic Additions to Nitroindoles -- 2.2. Nucleophilic Additions to & alpha;, & beta;-Unsaturated Nitrones -- 2.3. Pummerer Reactions to Create Spiro-Indolenines -- 2.4. Addition of Carbon Nucleophiles to Alkylideneindolium Ions -- 2.5. Pyridoindole-Based Quinone Methides -- 3. Nucleophilic Substitution Reactions of Indole -- 3.1. Vicarious Nucleophilic Substitutions -- 3.2. Ipso Substitution -- 3.3. SN2' -- References -- Metalation of Indole / Erin T. Pelkey -- 1. Introduction -- 2. Metalation Directed by Nitrogen Functionality -- 2.1. C2-Lithiation of N-Methylindoles -- 2.2. C2-Lithiation of N-(Arylsulfonyl)indoles -- 2.3. C2-Lithiation of N-(Carboalkoxy)indoles -- 2.4. C2-Lithiation of Indole-1-Carboxylic Acids -- 2.5. C2-Lithiation of Other N-(Substituted)indoles -- 2.6. C2 Metalation with Other Metals -- 2.7. C3-Lithiation -- Metal-Catalyzed Cross-Coupling Reactions for Indoles / Gordon W. Gribble -- 1. Introduction -- 2. Palladium-Catalyzed Cross-Coupling Reactions -- 2.1. Mori-Ban Indole Synthesis -- 2.2. Larock Indole Synthesis -- 2.3. Oxidative Coupling -- 2.4. Kumada Coupling -- 2.5. Negishi Coupling -- 2.6. Suzuki Coupling -- 2.7. Stille Coupling -- 2.8. Sonogashira Coupling -- 2.9. Heck Coupling -- 2.10. Carbonylation -- 2.11. C-N Bond Formation -- 2.12. Direct Arylation -- 3. Copper-Catalyzed Cross-Coupling Reactions -- 3.1. Selective N1-Arylation |
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Note continued: 3.2. Selective C2-Arylation -- 3.3. Selective C3-Arylation -- 4. Rhodium-Catalyzed Cross-Coupling Reactions -- 4.1. Selective C2-Arylation -- 4.2. Selective C3-Arylation -- 5. Iron-Catalyzed Cross-Coupling Reactions -- 6. Nickel-Catalyzed Cross-Coupling Reactions -- References -- Radical Reactions of Indole / Jeanese C. Badenock -- 1. Introduction -- 2. Intermolecular Radical Reactions -- 2.1. Radical Addition and Substitution Reactions of Indole -- 2.2. Radical Addition Reactions of Indolylacyl Radicals -- 3. Intramolecular Radical Reactions -- 3.1. Synthesis of the Indole Core -- 3.2. Synthesis of Spirooxindoles and Spiroindolines -- 3.3. Synthesis of Indole-Fused Five-Membered and Six-Membered Rings -- 3.4. Synthesis of Indole-Fused Seven-Membered and Eight-Membered Rings -- References -- [2+2], [3+2] and [2+2+2] Cycloaddition Reactions of Indole Derivatives / Steven J. Berthel -- 1. Introduction -- 2. [2+2] Cycloadditions -- 2.1. [2+2] Cycloadditions Between Indole Aryne Molecules and Olefins -- 2.2. [2+2] Photocycloaddition of Indoles and Olefins -- 2.3. [2+2] Cycloadditions of Indoles and Alkynes -- 2.4. [2+2] Cycloadditions of Indoles and Carbonyl Groups -- 3. Indole 2,3-Dipolar Cycloadditions -- 3.1. Indole Pyrrole Ring as Dipolarophile -- 3.2. Indole Phenyl Ring as Dipolarophile -- 3.3. Indole Pyrrole Ring as Dipole -- 4. [2+2+2] Cycloadditions -- 5. Conclusion -- References -- [4+2] Cycloaddition Reactions of Indole Derivatives / Fariborz Firooznia -- 1. Introduction -- 2. Indoles as Dienophiles in [4+2] Cycloaddition Reactions -- 2.1. Inverse Electron Demand Diels-Alder Reactions with Azadienes -- 2.2. Inverse Electron Demand Diels-Alder Reactions with Other Dienes -- 2.3. Inverse Electron Demand Diels-Alder Reactions in the Synthesis of Natural Products |
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Note continued: 2.4. Indoles as Dienophiles in "Normal" Electron Demand Diels-Alder Reactions -- 2.5. Cycloadditions Involving Indole Aryne Derivatives or Double Bonds in the Benzoid Portion of the Indole -- 3. Indole as Diene: 2-Vinylindoles -- 3.1. General Considerations: Regio and Stereochemistry -- 3.2. Application of [4+2] Reactions with 2-Vinylindoles to the Synthesis of "Linear" Indole Alkaloids -- 3.3. Application of [4+2] Reactions with 2-Vinylindoles to the Synthesis of Pyrrolo and Indolocarbazoles -- 3.4. Application of [4+2] Reactions with 2-Vinylindoles to the Synthesis of Vinca Alkaloids -- 3.5. 2-Alkynyl Indoles and 2-Allenylindoles as Dienes in Cycloaddition Reactions -- 4. Indole as Diene: 3-Vinylindoles -- 4.1. Simple 3-Vinylindole Systems -- 4.2. Application of Diels-Alder Reactions with 3-Vinylindoles in the Synthesis of Biscarbazoles -- 4.3. 3-Quinone-Indole Systems as Dienes -- 4.4. Application of Diels-Alder Reactions with 3-Vinylindoles in the Synthesis of Novel Pentacyclic Systems -- 4.5. Application of Diels-Alder Reactions with 3-Vinylindoles in the Synthesis of Indolocarbazoles and Pyrrolocarbazoles -- 4.6. Application of Diels-Alder Reactions with 3-Vinylindoles in the Synthesis of & beta; and & gamma;-Carboline Alkaloids -- 4.7. Tandem Reactions and Multicomponent Syntheses -- 5. Indoles as Dienes: Noncyclic Indolo-2,3-quinodimethanes -- 5.1. Indolo-2,3-quinodimethanes from Bis(bromomethyl)indoles -- 5.2. Indolo-2,3-quinodimethanes from Gramine Derivatives -- 5.3. In Situ Generated Indolo-2,3-dienolates as Indolo-2,3-quinodimethanes -- 5.4. Indolo-2,3-quinodimethanes from 3-Cyanomethyl-2-vinylindoles -- 5.5. Indolo-2,3-quinodimethanes from Intramolecular Heck Reactions of & alpha;-Phosphono Enecarbamates -- 5.6. Indolo-2,3-quinodimethanes from Intramolecular Heck Reactions of & alpha;-Phosphono Enecarbamates |
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Note continued: 5.7. Multicomponent Synthesis with Indolo-2,3-quinodimethanes -- 6. Indoles as Dienes: Fused Cyclic Indolo-2,3-quinodimethanes -- 6.1. Furo[3,4-b]indoles as Indolo-2,3-quinodimethanes Analogs -- 6.2. Pyrrolo[3,4-b]indoles as Indolo-2,3-quinodimethanes Analogs -- 6.3. Pyrano[3,4-b]indolones as Indolo-2,3-quinodimethanes Analogs -- 6.4. Indolo-3-sulfolenes as Indolo-2,3-quinodimethanes Analogs -- 6.5. Indolo-4,5-quinodimethane Analogs -- 7. Conclusion -- References -- Oxindoles and Spirocyclic Variations: Strategies for C3 Functionalization / Jonathon S. Russel -- 1. Introduction -- 2. Methods for Quaternization at Oxindole C3 -- 2.1. Construction of All-Carbon Quaternary Centers -- 2.2. Construction of Heteroatom Containing C3 Quaternary Centers -- 3. Methods for Spirocyclization at Oxindole C3 -- 3.1. Synthesis of All-Carbon C3 Spirocenters -- 3.2. Synthesis of Heteroatom Containing C3 Spirocycles -- 4. Natural Product Total Synthesis -- 4.1. Oxindole Intermediates in Natural Product Synthesis -- 4.2. Oxindole Natural Product Total Synthesis -- 5. Concluding Remarks -- References -- Advances in the Total Syntheses of Complex Indole Natural Products / Liangfeng Fu -- 1. Introduction -- 2. Indole Alkaloids with Potent Biological Activity -- 2.1. Actinophyllic Acid -- 2.2. Communesin F and Perophoramidine -- 2.3. Diazonamide A -- 2.4. Minfiensine -- 2.5. Stephacidin B -- 2.6. Yatakemycin -- 3. Other Complex Indole Alkaloids -- 3.1. Chartelline C -- 3.2. Haplophytine -- 3.3. Kapakahine B -- 3.4. ( -- )-Penitrem D -- 3.5. Phalarine -- 3.6. Quadrigemine C and 11,11'-Dideoxyvertillin A -- 3.7. Welwitindolinone A -- References |
| Summary |
Yong-Jin Wu New Indole-Containing Medicinal Compounds Timothy C. Barden Indoles: Industrial, Agricultural and Over-the-Counter Uses Richard J. Sundberg Electrophilic Substitution Reactions of Indoles Tara L.S. Kishbaugh Reactions of Indole with Nucleophiles Erin Pelkey Metalation of Indole Jie Jack Li "Gordon W. Gribble Metal-Catalyzed Cross-Coupling Reactions for Indoles Jeanese C. Badenock Radical Reactions of Indole Fariborz Firooznia "Robert F. Kester "Steven J. Berthel [2+2], [3+2] and [2+2+2] Cycloaddition Reactions of Indole Derivatives Steven J. Berthel "Fariborz Firooznia "Robert F. Kester [4+2] Cycloaddition Reactions of Indole Derivatives Jonathon S. Russel Oxindoles and Spirocyclic Variations: Strategies for C3 Functionalization Liangfeng Fu Advances in the Total Syntheses of Complex Indole Natural Products |
| Bibliography |
Includes bibliographical references and index |
| Notes |
English |
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Print version record |
| Subject |
Indole.
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Indole
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| Form |
Electronic book
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| Author |
Gribble, Gordon W.
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Badenock, J. C. (Jeanese C.)
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| ISBN |
9783642157332 |
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3642157335 |
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